GLADWELL

Let's set the record straight on Jennifer Aniston. She was not hitting on me. I think she was bored because her friends hadn't arrived yet. She just wanted to make conversation. And what was my excuse? I don't really have one. I was trying to work, and I wasn't wearing my glasses, and who on earth thinks Jennifer Aniston is going to sit down next to them in some random cafe in Miami and start chatting away? So I gave her that don't-bother-me glare, and then about five minutes passed and I thought to myself, "You know, she was really cute." And another five minutes passed and I thought, "You know, she looks really familiar." And another five minutes passed and I thought, "You idiot." And by then it was too late, of course. The window of opportunity for a woman like that is 45 seconds, max. By the time I got the check, I think she'd already started dating John Mayer. Sigh. I had a similar random encounter with Baron Davis once in the lobby of a hotel in Chicago, only I recognized him. I think you can safely say you've watched too much "SportsCenter" when you whiff on Jennifer Aniston and spot Baron Davis from across a crowded room.

You're right. I am a bit obsessed with the full-court press at the moment. I just did a story for The New Yorker about how underdogs beat favorites, which had a lot about basketball in it. For the story, I went down to Louisville and had a long chat with Rick Pitino. He argued that the press is the best chance an underdog has of being competitive with stronger teams, and I think his record proves the case. That Providence team he took to the Final Four in 1984 has to have been just about the least talented team EVER to reach that level. (One of the forwards on that team was Dave Kipfer, who grew up just down the road from me, in the southwestern Ontario Mennonite country. He was considered slow for our high school league.) Then, of course, Pitino takes one of his first Louisville teams to the Final Four in 2005 and this season's team to the Elite Eight, and no one's going to argue that either of those teams were filled with future Hall of Famers. Given that, then, why do so few underdog teams use the press? Pitino's explanation is that it's because most coaches simply can't convince their players to work that hard. What do you think of that argument?

There are two other things here that fascinate me. After my piece ran in The New Yorker, one of the most common responses I got was people saying, well, the reason more people don't use the press is that it can be beaten with a well-coached team and a good point guard. That is (A) absolutely true and (B) beside the point. The press doesn't guarantee victory. It simply represents the underdog's best chance of victory. It raises their odds from zero to maybe 50-50. I think, in fact, that you can argue that a pressing team is always going to have real difficulty against a truly elite team. But so what? Everyone, regardless of how they play, is going to have real difficulty against truly elite teams. It's not a strategy for being the best. It's a strategy for being better. I never thought Louisville -- or, for that matter, Missouri -- had a realistic shot at winning it all in the NCAAs this year. But if neither of those teams pressed, they wouldn't have been there in the first place. I wonder if there isn't something particularly American in the preference for "best" over "better" strategies. I might be pushing things here. But both the U.S. health-care system and the U.S. educational system are exclusively "best" strategies: They excel at furthering the opportunities of those at the very top end. But they aren't nearly as interested in moving people from the middle of the pack to somewhere nearer the front.

The other, related question is whether you can ever truly run the press with elite players. Pitino did it once, with that stacked 1996 Kentucky team. But I think even he realizes that was a once-in-a-lifetime achievement. Think about it: He got Antoine Walker to play defense for 94 feet. And John Wooden used the press a lot with some of his great teams at UCLA. But he was John Wooden, and that was another era. Realistically, could you convince a couple of McDonald's All-Americans, who have been coddled and indulged their whole lives, to play that way today? When we were talking, Pitino called over Samardo Samuels, who is, of course, Jamaican -- his point being that this was his ideal kind of player, someone who substituted for a lack of experience with a lot of hunger. There is something weird, isn't there -- and also strangely beautiful -- about a coach who deliberately seeks out players who aren't the most talented? I know you have very, um, complicated feelings about Pitino. I love the man.

The biggest question, though, is whether there is any way to apply the press at the pro level. Thoughts?

SIMMONS

You're preaching to the floor-burn choir. I watched the press succeed (to a decent degree) during Pitino's first season in Boston, and attended most of those home games. Of course, Coach P undermined his own cause by panic-trading rookie Chauncey Billups after 50 games to acquire Kenny Anderson, an all-offense guard who was making $10 million a season and had no interest in sprinting for 40-plus minutes, especially when he hadn't yet sweated out all the Courvoisier from the night before. Still, three things happened during that 50-game stretch to make me believe presses could work at the professional level.

1. That 1997-98 Celtics team overachieved. Pitino made so many preseason moves that they started with just three incumbents (Antoine Walker, Dee Brown and Dana Barros) and played 19 different guys in all, but they still finished 36-46 with a group of rookies and castoffs, as well as Antoine shooting 42 percent, making 292 turnovers and offending approximately 572 officials as their crunch-time guy. Before the Billups trade, they had one really nice pressing unit: two athletic rookies (Billups and Ron Mercer), young Bruce Bowen, Walter McCarty (the best cog in the history of Pitino's press, as the coach told you) and either Travis Knight or Andrew DeClercq (two agile, coachable and extremely pale big men). This group wreaked havoc a few times. I remember attending one November home game during which they dismantled the Nuggets with it. Just for kicks, I looked it up on basketball-reference.com. The Celtics won 96-86. They forced 29 turnovers. They had a whopping 16 steals. Denver's point guard (a young Bobby Jackson) committed eight turnovers. Seven Celtics finished with two-plus steals. If Pitino had just kept that nucleus -- Walker, Billups, Mercer, Barros, Brown, McCarty, Bowen, Knight and DeClercq -- been patient and allowed his young guys to take their lumps, we would have had something (and remember, Pierce was coming in the '98 draft). So frustrating. Pitino took the concept of "own worst enemy" to new heights.

Jim McIsaac/Getty ImagesWalter McCarty was an ideal cog in the full-court press.

2. Once Walker got his big contract (a max extension before the '98-99 season), suddenly he wanted to jog around and jack up bad 3-pointers, and since he was guaranteed $71 million, who was going to talk him out of it? This proved that a press can only work professionally if you are using guys who carry 10s and 20s in their wallets instead of 100s. Which leads me to the following tweak, something that Pitino even mentioned when you spent time with him.

With a 12-man roster, you'd only need to train five or six guys to pull off that press. Let's say next season's Bulls trained the following five: Joakim Noah, Ty Thomas, Kirk Hinrich, Lindsey Hunter and Generic Athletic/Hungry Swingman X. They practice and practice until they become a well-oiled pressing machine. For the first five minutes of every second and fourth quarter, they unleash that killer press on their opponents who, by the way, would be playing backups during that time, making it even more effective. Wouldn't that be an ENORMOUS advantage? Wouldn't that swing a few games? Wouldn't opponents dread playing them? Wouldn't opponents have to waste practice time preparing to break that press? Wouldn't it be even better at home with the Bulls flying around and their fans going bonkers? The key would be not putting "press miles" on your top guys and your wealthiest guys (who would never be totally invested because, again, they're really, really wealthy and don't need this crap). In this scenario, the Bulls wouldn't press with Rose, Deng, Brad Miller, Ben Gordon or even John Salmons if they could help it. Which brings me to my third point.

3. You can easily find 10th, 11th and 12th men to make that press work. You know how many athletic swingmen are out there? Oodles. There's always another Dahntay Jones or Josh Powell killing himself in the D-League hoping for a chance. It's just a logical way to use your roster. You could build the press around one scorer (one of your top-five guys) and the ninth, 10th, 11th and 12th guys on your team. Like the 2008-09 Clippers. Couldn't they have pressed for 10 minutes a game with Al Thornton, Mike Taylor, DeAndre Jordan, Fred Jones and Mardy Collins? Why the hell not? Oh, wait, I forgot they have a dunce as a coach.

The bigger point: NBA teams rarely, if ever, think outside the box, and that's one of at least 50 reasons why I could succeed as a GM. Over the course of an 82-game season, a killer press might swing five or six games. If I ran an NBA team, I would study tapes of those first 50 games the '97-98 Celtics played with Billups. Carefully. They were 21-24 through 45 games with the youngest team in the league during an extremely competitive season. Hmmmmmm.

GLADWELL

Let me get this straight. Pitino uses the press at Boston for 50 games and achieves a surprising result. And an entire league full of very thoughtful and knowledgeable coaches watch him do that, and in the past decade not a single one has even tried to follow Pitino's example?

SIMMONS

Yup. Although the late '90s were the peak of the NBA's Too Young Too Much Too Soon Era: too many young guys getting paid too much too soon, and handling it about as well as your average group of successful child actors getting their first fake IDs. This stretch was dominated by posses, tattoos, crotch-grabs, sneers, coach-choking and everything else; just a bunch of immature guys who carried themselves like superstars even though they hadn't done squat. Really, 1993-99 was one of the two "Wasted Eras of Young Talent," along with 1978-86 (the coke era). So the thinking was probably "I can't even get these guys to run a high screen without them glaring at me or MF-ing me I'm gonna get them to press?" Players are much more humble and responsible and self-aware these days, so it might have a better chance.

GLADWELL

Still, is there any other industry in the world (well, outside of Detroit) so terrified of innovation? I went to see a Lakers-Warriors game earlier this season, and it was abundantly clear after five minutes that the Warriors' chances of winning were, oh, no better than 10 percent. Why wouldn't you have a special squad of trained pressers come in for five minutes a half and press Kobe and Fisher? Worst-case scenario is that you exhaust Kobe, and make him a bit more vulnerable down the stretch. Best case is that you rattle the Lakers and force a half-dozen extra turnovers that turn out to be crucial. And if you lose, so what? You were going to lose anyway. When you become GM of the Timberwolves, I'm guessing you'll put the special-press-squad concept into effect immediately.

SIMMONS

Yes. In a heartbeat. It's one of the few roster advantages you have: By using that killer press, you are turning your 10th, 11th and 12th men into assets instead of guys who are measured by their ability to execute chest-bumps and feign excitement over someone else's success. So yeah. The killer press is on the agenda.

GLADWELL

Would you pay Pitino $4 million to do a one-year consultancy at Minnesota, to set up and train the squad? And -- since I know you love lists -- who would be your all-time full-court press team? One rule: you can't pick people who would otherwise be considered all-time greats. So no Jordan or Pippen.

SIMMONS

I'll give you two different teams. If you went with superstars or All-Stars, you'd go with 1993-94 David Robinson, '88-89 Dennis Rodman, '91-92 Scottie Pippen, 2008-09 LeBron and 1991-92 Jordan. Good luck bringing the ball up against those five guys. You'd have a better chance of drinking 24 beers, then trying to pee from midcourt into one of the baskets.

WireImage.comWe've definitely got to have the Christies on our all-full-court press squad.

For non-superstars, I'd go with this group: '97-98 Walter McCarty, 2002-03 Lindsey Hunter, '03-04 Andrei Kirilenko, '01-02 Ben Wallace, and '00-01 Doug Christie (narrowly edging '02-03 Bruce Bowen only because we get Jackie Christie cheering the press from the stands as part of the deal). When you think how frightening those five guys would have been -- and by the way, none were lottery picks except Hunter -- it makes you wonder: Would it be that hard to find a poor man's version of the five guys above, bring in Pitino for two weeks as an expensive consultant to train them and a specific assistant to handle it, then cultivate it throughout the season? More importantly, why wouldn't you try? Or at least investigate it?

GLADWELL

I feel the same way about the attitude of professional football teams toward the no-huddle offense. Right now, great teams (such as the Colts and Patriots) use the no-huddle selectively, as a way to maximize their dominance. But why don't bad teams use it? If you were the Lions, why not run the no-huddle this season? Why not put together a lighter, better-conditioned offensive line and a radically simplified playbook and see what happens? It's not as if you are risking a Super Bowl if it backfires. Your offensive line is lousy anyway, so there's no harm in tearing it down, and your fans aren't going to turn on you if you get killed while you work out the kinks. Last I checked, your fans have already turned on you. On the plus side, maybe the no-huddle exhausts the other team's defense so much you slow down their pass rush in the second half. And maybe giving your quarterback a bit more autonomy helps develop his knowledge of the game, and his leadership skills.

The consistent failure of underdogs in professional sports to even try something new suggests, to me, that there is something fundamentally wrong with the incentive structure of the leagues. I think, for example, that the idea of ranking draft picks in reverse order of finish -- as much as it sounds "fair" -- does untold damage to the game. You simply cannot have a system that rewards anyone, ever, for losing. Economists worry about this all the time, when they talk about "moral hazard." Moral hazard is the idea that if you insure someone against risk, you will make risky behavior more likely. So if you always bail out the banks when they take absurd risks and do stupid things, they are going to keep on taking absurd risks and doing stupid things. Bailouts create moral hazard. Moral hazard is also why your health insurance has a co-pay. If your insurer paid for everything, the theory goes, it would encourage you to go to the doctor when you really don't need to. No economist in his right mind would ever endorse the football and basketball drafts the way they are structured now. They are a moral hazard in spades. If you give me a lottery pick for being an atrocious GM, where's my incentive not to be an atrocious GM?

I think the only way around the problem is to put every team in the lottery. Every team's name gets put in a hat, and you get assigned your draft position by chance. Does that, theoretically, make it harder for weaker teams to improve their chances against stronger teams? I don't think so. First of all, the principal engine of parity in the modern era is the salary cap, not the draft. And in any case, if the reverse-order draft is such a great leveler, then why are the same teams at the bottom of both the NFL and NBA year after year? The current system perpetuates the myth that access to top picks is the primary determinant of competitiveness in pro sports, and that's simply not true. Success is a function of the quality of the organization.

Another more radical idea is that you do a full lottery only every second year, or three out of four years, and in the off year make draft position in order of finish. Best teams pick first. How fun would that be? Every meaningless end-of-season game now becomes instantly meaningful. If you were the Minnesota Timberwolves, you would realize that unless you did something really drastic -- like hire some random sports writer as your GM, or bring in Pitino to design a special-press squad -- you would never climb out of the cellar again. And in a year with a can't-miss No. 1 pick, having the best record in the regular season becomes hugely important. What do you think?

Bill Simmons (@BillSimmons) is the editor-in-chief of Grantland and the author of the New York Times no. 1 best-seller The Book of Basketball. For every Simmons column and podcast, log on to Grantland. To send him an e-mail, click here.